The present invention provides a carbon-containing material, a process for its preparation, and its use.
EP 0569503 discloses a process for the surface modification of carbon-containing materials with aromatic groups by the electrochemical reduction of a diazonium salt.
Furthermore, it is known that carbon black can be provided with organic groups by linking the organic groups to the carbon-containing material via reaction with diazonium salts that are obtained by diazotization (WO 96/18690) or bonding the organic groups to the carbon black by reactions with radical producers (Ohkita K., Tsubokawa N., Saitob E., Carbon 16 (1978) 41), DE 10012784.3) or via cycloaddition reactions (DE 10012783.5, JP 11315220 A).
Known processes have the following disadvantages:
Apart from toxic and flame-supporting sodium nitrite, the non-ionic organic nitrites which can also be used for diazotisation are toxic and readily inflammable. Residues of nitrites (gegenions, alkyl groups) remain, unbonded, as impurities in the carbon black.
The use of a nitrite in acid medium is required in order to perform a diazotisation reaction. Toxic nitrogen oxides may thus also be produced.
Radical producers are thermally or photochemically labile, potentially explosive and may lead to chain reactions which are difficult to control.
The synthesis and purification of the corresponding precursors of radical producers sometimes proceeds via toxic substances or those which cause a nuisance due to odor.
The elimination of nitrogen which takes place during cyclisation reactions with nitrogen heterocyclic compounds can lead to sudden, explosion-like increases in volume or rises in pressure which makes reaction management substantially more difficult.
It is an object of the invention to provide a carbon-containing material with organic groups, wherein
modification of the carbon-containing material can be varied in such a way that the groups are located directly on the surface of the carbon-containing material and/or may also be displaced well away from the surface of the carbon-containing material,
modification of the carbon-containing material proceeds without the need for preliminary reactions such as activation by starters,
reactions with the modification agents used in accordance with the invention proceed thermally and catalysts (for example Lewis acids) are not required,
due to the chemical properties of the modification agents used in accordance with the invention, no problematic side reactions or difficult to control chain reactions can take place,
the resulting carbon-containing material is not contaminated with acids, salts and the like so no purification of the carbon-containing material is required,
the carbon-containing material does not have to be dried with the consumption of large amounts of energy,
no toxic waste gases are produced during modification, and/or
no solvents, or only small amounts of readily removable solvents, are required.
The invention provides a carbon-containing material with organic groups, wherein this is obtainable by reaction of the carbon-containing material with organic compounds of the general formula 1: 
where R1, R2 and R3 are identical or different and comprise H or alkyl or aryl groups with acceptor or donor substituents and/or hydrophilic or hydrophobic groups or R1 and R3 form a cyclic system with the three nitrogen atoms and R2 comprises H or alkyl or aryl groups with acceptor or donor substituents and/or hydrophilic or hydrophobic groups.
The present invention also provides a composition, comprising the carbon-containing material described above and at least one member selected from the group consisting of rubber, plastics, printing inks, inks, inkjet inks, lacquers, toners and colorants, bitumen, concrete, other constructional materials, and paper.
The present invention also provides a method of making the composition described above, comprising incorporating the carbon-containing material into a member selected from the group consisting of rubber, plastics, printing inks, inks, inkjet inks, lacquers, toners and colorants, bitumen, concrete, other constructional materials, and paper.
The present invention also relates to a dispersion, which contains the carbon-containing material with organic groups described above.
The present invention also provides an ink, lacquer, toner, or colorant contain the dispersion described above.
The present invention also provide a method of making the ink, lacquer, toner or colorant described above, comprising incorporating the dispersion in to the ink, lacquer, toner, or colorant.
The present invention also provides compound represented by the formula 2 or 3: 
wherein
X is H, metaln+, or N+(R4)4,
Y is H, metaln+, or N+(R4)4,
n is 1, 2, or 3,
u is 1, 2, or 3, and
R4 is H or an alkyl or aryl group or a functionalized alkyl group or a functionalized aryl group.
A more complete appreciation of the invention and many of the attendant advantages thereof will be readily obtained as the same becomes better understood by reference to the following Figures in conjunction with the detailed description below.